4.7 Article

Electron-Deficient Polycyclic π-System Fused with Multiple B←N Coordinate Bonds

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 3, Pages 2100-2106

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02052

Keywords

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Funding

  1. National Science Foundation [1654029]
  2. Qatar National Priority Research Program [NPRP11S-1204-170062]
  3. Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy [DE-AC02-05CH11231]
  4. DOE Office of Science [DEAC02-06CH11357]
  5. Direct For Mathematical & Physical Scien
  6. Division Of Materials Research [1654029] Funding Source: National Science Foundation

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An extensive polycyclic pi-system with 23 fused rings was synthesized via a highly efficient borylation reaction, forming four B-N covalent bonds and four B <- N coordinate bonds. The B <- N coordinate bonds not only lock the backbone into a near-coplanar conformation but also decrease the LUMO energy level, demonstrating the dual utility of this strategy for the synthesis of rigid polycyclic molecules and the development of n-type conjugated materials for organic electronics and photovoltaics.
An extensive polycyclic pi-system with 23 fused rings is synthesized via a highly efficient borylation reaction, in which four B-N covalent bonds and four B <- N coordinate bonds are formed in one pot. B <- N coordinate bonds not only lock the backbone into a near-coplanar conformation but also decrease the LUMO energy level to around -3.82 eV, demonstrating the dual utility of this strategy for the synthesis of extensive rigid polycyclic molecules and the development of n-type conjugated materials for organic electronics and organic photovoltaics.

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